Due to a complicated mix of insecurity and misanthropy, I gave up formal bicycle racing more than a decade ago. I kept reminding myself of this wise decision last fall, after the tight paceline set by the five other racers on my team destroyed my ability to consume solids and I spent 70 miles guzzling a sticky cocktail of Gatorade and Mountain Dew.

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But I wasn't telling myself, as you might expect, that I'd never race again once I finished that day. I was thinking just the opposite: that I couldn't wait to do this again—because while we were racing as hard as I ever had back when I took it all too seriously, we were having more fun than I'd ever had in that era.

The Rapha Gentlemen's Race was a 137-mile, unsanctioned, invite-only contest to ride from Oregon's northern coast to downtown Portland as quickly as possible. Formally there was no race at all. The waiver we signed to gain entry mentioned only "the Activity," and Slate Olson, the founder of the Gentlemen's Race and Rapha's U.S. general manager, said those of us on the road were to be referred to as a "coincidence." (During last year's version, Olson says, a police officer who stopped and questioned him was highly skeptical that so many groups of cyclists riding in such an organized fashion could really be construed as a coincidence, but ultimately waved him on.) There were no road closures, just hot-pink hashes marking the course. There were no marshals or rules. The only obligations—outside of riding safely—were that each team had to pass through two checkpoints along the course and fill up a disposable camera, issued at the start, with snapshots from the road. Twenty-three teams showed up, from around the Pacific Northwest and from as far afield as Oklahoma and California. Every rider paid a $20 entry fee and got a T-shirt and a Rapha-branded church key. Every team had to contribute a six-pack of beer to the prize pool, which also included Rapha jerseys for the winners but nothing else.

Thanks to Rapha's significant alternative marketing savvy, the Gentlemen's Race is a well-documented example of the recent groundswell in similar events. Their very nature makes an objective and accurate count impossible, but unsanctioned, informal, underground races outside the governance of any officiating body are occurring with more frequency in every state and discipline—from road and mountain bike events to mixed-terrain adventures and the by-now classic urban, messenger-style alley cats.

Many demand far more of the rider than the average four-corner criterium or short-track circuit. The Trans-Iowa Race and the Dirty Kanza 200 stack multiple centuries on gravel-strewn country roads, while the Tour Divide spans weeks and two countries. Some unsanctioned races, like the Singlespeed World Championships and Single Speed Cyclocross World Championships, are as much about the party as the competition. But despite—or because of—this, top-level pros still partake. Giant's Adam Craig has podiumed at both singlespeed events. And team Kona's Twin Towers, Ryan Trebon and Barry Wicks, are stalwarts of the singlespeed cyclocross race (the latter in a gold-lame Speedo). Winners at both championships are rewarded with a trademark tattoo—better not win if you want to keep your hide pristine.